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Metformin

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Name

Metformin

EINECS 211-517-8
CAS No. 657-24-9 Density 1.28 g/cm3
PSA 88.99000 LogP 0.25650
Solubility N/A Melting Point 199-200 °C
Formula C4H11N5 Boiling Point 224.1 °C at 760 mmHg
Molecular Weight 129.165 Flash Point 89.3 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 657-24-9 (Metformin) Hazard Symbols N/A
Synonyms

Biguanide,1,1-dimethyl- (6CI,8CI);1,1-Dimethylbiguanide;Cidophage;DMGG;Dimethylbiguanide;Emiphage;Ficonax;Fluamine;Flumamine;Gliguanid;Glucofine;Haurymelin;Metiguanide;Metphage;N,N-Dimethyl-imidodicarbonimidic diamide;N,N-Dimethylbiguanide;N,N-Dimethyldiguanide;N1,N1-Dimethylbiguanide;NNDG;N'-Dimethylguanylguanidine;Siofor;Imidodicarbonimidicdiamide, N,N-dimethyl-;

Article Data 49

Metformin Synthetic route

1115-70-4

metformin hydrochloride

657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 0.5h;100%
With sodium hydroxide In water at 20℃; for 0.5h;99%
With sodium hydroxide In ethanol for 5h;99%

N,N-dimethylimidodicarbonimidic diamide hydrochloride

657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With sodium hydroxide In isopropyl alcohol at 0 - 40℃; for 18.2h; Temperature; Solvent;93%
With sodium hydroxide In isopropyl alcohol at 39.84℃; for 3h;
With sodium In ethanol at 60℃; for 1h; Reagent/catalyst; Solvent; Temperature;
506-59-2

N,N-dimethylammonium chloride

127099-85-8, 780722-26-1

N-Cyanoguanidine

657-24-9

dimethylbiguanide

Conditions
ConditionsYield
at 130 - 140℃;
In butan-1-ol for 6h; Reflux;
127099-85-8, 780722-26-1

N-Cyanoguanidine

dimethylamine-

dimethylamine-

657-24-9

dimethylbiguanide

Conditions
ConditionsYield
at 160℃;
124-40-3

dimethyl amine

127099-85-8, 780722-26-1

N-Cyanoguanidine

A

657-24-9

dimethylbiguanide

B

N,N-dimethyl-guanidine

N,N-dimethyl-guanidine

Conditions
ConditionsYield
at 180℃; beim Erhitzen des Hydrochlorids;
1170667-82-9

N1,N1-dimethyl-S-cyclohexyl-N4-thiohydroxybiguanidine

657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With hydrogenchloride In water at 37℃; pH=1.0; Reactivity;
1170667-83-0

N1,N1-dimethyl-S-phenyl-N4-thiohydroxybiguanidine

657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With human serum at 37℃; pH=7.4; Reactivity; Enzymatic reaction; Aqueous phosphate buffer;
1378856-94-0

N,N-dimethylebiguanidinium chloride

657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 2h;
657-24-9

dimethylbiguanide

1200-22-2

(R)-1,2-dithiolane-3-pentanoic acid

959986-37-9

N,N-dimethylimidodicarbonimidic diamide R-(+)-lipoate

Conditions
ConditionsYield
In methanol for 2h; Product distribution / selectivity;100%
In acetonitrile for 0.166667h; Product distribution / selectivity;95%
In acetone for 0.166667 - 0.5h; Product distribution / selectivity;95%
In methanol; acetone for 0.333333h; Product distribution / selectivity;

((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl)-L-leucyl-L-leucinate

657-24-9

dimethylbiguanide

amino(3,3-dimethylguanidino)methaniminium (S)-2-((S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)-4-methylpentanamido)-4-methylpentanoate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h;100%

Metformin Specification

1. Introduction of Metformin
Metformin is one kind of white or off-white crystal powder. The IUPAC name of 1,1-Dimethylbiguanide is 3-(diaminomethylidene)-1,1-dimethylguanidine. The classification codes are Antidiabetic; Drug / Therapeutic Agent; Hypoglycemic agents; Mutation data; Reproductive Effect. When heated to decomposition it emits toxic fumes of NOx. Besides, it is freely soluble as HCl salt.

2. Properties of Metformin
The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.82; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -3.82; (4)ACD/LogD (pH 7.4): -3.82; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.576; (13)Molar Refractivity: 33.35 cm3; (14)Molar Volume: 100.7 cm3; (15)Polarizability: 13.22×10-24 cm3; (16)Surface Tension: 50.8 dyne/cm; (17)Enthalpy of Vaporization: 46.06 kJ/mol; (18)Vapour Pressure: 0.0929 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 3; (21)Exact Mass: 129.101445; (22)MonoIsotopic Mass: 129.101445; (23)Topological Polar Surface Area: 91.5; (24)Heavy Atom Count: 9; (25)Complexity: 132.

3. Structure Descriptors of Metformin
People can use the following data to convert to the molecule structure.
(1)SMILES:[N@H]=C(\N=C(/N)N)N(C)C
(2)InChI:InChI=1/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
(3)InChIKey:XZWYZXLIPXDOLR-UHFFFAOYAB
(4)Canonical SMILES : CN(C)C(=N)N=C(N)N

4. Toxicity of Metformin
The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LD50 parenteral 5gm/kg (5000mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archiwum Immunologii i Terapii Doswiadczalnej. Vol. 2, Pg. 1, 1954.
guinea pig LD50 subcutaneous 146mg/kg (146mg/kg)   Medicina Experimentalis. Vol. 8, Pg. 237, 1963.
man TDLo oral 321mg/kg/15D- (321mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"
New England Journal of Medicine. Vol. 339, Pg. 1860, 1998.
 
mouse LD50 intraperitoneal 247mg/kg (247mg/kg)   Journal of Medicinal Chemistry. Vol. 10, Pg. 521, 1967.
mouse LD50 oral 1450mg/kg (1450mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 subcutaneous 230mg/kg (230mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archiwum Immunologii i Terapii Doswiadczalnej. Vol. 2, Pg. 1, 1954.
women TDLo oral 191mg/kg/9D-I (191mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA
Postgraduate Medical Journal. Vol. 76, Pg. 125, 2000.
 

5. Physical Properties of Metformin

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -2.640 (none)   EST
Atmospheric OH Rate Constant 1.53E-10 cm3/molecule-sec 25 EST

6. Uses of Metformin
Metformin is a biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. It can react with imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester to get 6-imidazo[1,2-a]pyridin-2-yl-N,N-dimethyl-[1,3,5]triazine-2,4-diamine. This reaction needs reagent sodium methoxide and solvent methanol. The yield is 36%.

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